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Abandoned drugs
Paroxypropione
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Paroxypropione

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Paroxypropione
Paroxypropione.svg
Clinical data
Trade names Frenantol, Frenormon, Hypophenon, Paroxon, Possipione, Profenone, others
Other names Paraoxypropiophenone; H-365; NSC-2834; 4'-Hydroxypropiophenone; Ethyl p-hydroxyphenyl ketone; p-Propionylphenol; Paroxypropiophenone; Parahydroxypropiophenone; PHP
Drug class Nonsteroidal estrogen; Antigonadotropin
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 1-(4-hydroxyphenyl)-1-propanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.676
Chemical and physical data
Formula C9H10O2
Molar mass 150.177 g·mol−1
3D model (JSmol)
  • CCC(=O)c1ccc(cc1)O
  • InChI=1S/C9H10O2/c1-2-9(11)7-3-5-8(10)6-4-7/h3-6,10H,2H2,1H3
  • Key:RARSHUDCJQSEFJ-UHFFFAOYSA-N

Paroxypropione, also known as paraoxypropiophenone, is a synthetic nonsteroidal estrogen which has been used medically as an antigonadotropin in Spain and Italy but appears to no longer be marketed. It was first synthesized in 1902. The antigonadotropic properties of the drug were discovered in 1951 and it entered clinical use shortly thereafter.

Pharmacology

Pharmacodynamics

Paroxypropione is closely related structurally to p-hydroxybenzoic acid and parabens such as methylparaben, and also bears a close resemblance to diethylstilbestrol (which, in fact, produces paroxypropione as an active metabolite) and alkylphenols like nonylphenol, all of which are also estrogens. The drug possesses relatively low affinity for the estrogen receptor and must be given at high dosages to achieve significant estrogenic and antigonadotropic effects, for instance, 0.8 to 1.6 g/day. It possesses 0.1% of the estrogenic activity and less than 0.5% of the antigonadotropic potency of estrone.

Chemistry

Synthesis

The highest reported yield, approximately 96%, is from the between phenol and propionyl chloride. The mechanism is likely to involve initial esterification to give phenyl propionate, which then undergoes a Fries rearrangement.

Derivatives

Paroxypropione is a precursor in the chemical synthesis of diethylstilbestrol and dienestrol.

Society and culture

Names

Brand names Frenantol, Frenormon, Hypophenon, Paroxon, Possipione, Profenone, numerous others; former developmental code name NSC-2834), also known as paroxypropiophenone (P.O.P.) or 4'-hydroxypropiophenone.

Research

Paroxypropione was studied and used in the treatment of breast cancer.

Further reading

  • Gustavo RP (July 1958). "[Anti-gonadotropic action of possipione]" [Anti-gonadotropic action of possipione]. Quaderni di Clinica Ostetrica e Ginecologica (in Italian). 13 (7): 307–15. PMID 13579130.

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